Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging. Issue 40 (23rd August 2019)

• Record Type: Journal Article
• Authors: Liu, Feng; Shi, Xiao; Liu, Xianjun; Wang, Fenglin; Yi, Hai-Bo; Jiang, Jian-Hui
• Is Part Of: Chemical science. Volume 10:Issue 40(2019)
• Page Start: 9257
• Page End: 9264
• Publication Date: 2019-08-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc02764e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel NIR rhodol derivative is engineered for the development of high-contrast activatable photoacoustic imaging based on generally applicable ring-opening responsiveness. Abstract : Molecular probes that enable high-contrast photoacoustic (PA) imaging of cellular processes are valuable tools for in vivo studies. Design of activatable PA probes with high contrast remains elusive. We develop a new NIR rhodol derivative, Rhodol-NIR, with a large extinction coefficient, low quantum yield and structural switching from a 'ring-open' form to a 'closed' spirolactone upon esterification. This structural transition, together with the ideal photophysical properties, enables the development of activatable probes for high-contrast PA imaging via a target-specific de-esterification reaction. This strategy is demonstrated using a PA probe designed for a tumor biomarker, human NAD(P)H: quinone oxidoreductase isozyme 1 (hNQO1), which affords high contrast and excellent sensitivity for PA detection and imaging of hNQO1 in living cells and animals. The strategy can provide a new paradigm for engineering activatable PA probes for high-contrast imaging.